First Stereoselective Synthesis of (1R,2R,4R)- and (1S,2R,4S)-2-Substituted-1-azabicyclo[2.2.1]heptanes

被引：2

作者：

Etayo, Pablo ^{[1
]}

Badorrey, Ramon ^{[1
]}

Diaz-de-Villegas, Maria D. ^{[1
]}

Galvez, Jose A. ^{[1
]}

机构：

[1] Univ Zaragoza, Inst Univ Catalisis Homogenea, Dept Quim Organ, Inst Ciencia Mat Aragon,CSIC, E-50009 Zaragoza, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 09期

关键词：

Asymmetric synthesis; Ketones; Nitrogen heterocycles; Diastereoselectivity; ALPHA-METALATED ISOCYANIDES; WADSWORTH-EMMONS REACTION; HOMOLOGATION; KETONES;

D O I：

10.1002/ejoc.200801216

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first stereoselective synthesis of two diastereomeric 1-azabicyclo[2.2.1]heptanes substituted at the 2-position from an easily accessible (R)-2-substituted-4-piperidone is reported. The synthetic route involves the asymmetric one-carbon homologation of a chiral ketone followed by an intramolecular S(N)2-type cyclisation and led to target compounds in high overall yield by using a simple procedure in which purification of the intermediate compounds is not required. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：1372 / 1376

页数：5

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